2-debenzoyl-2-(3-methylbutanoyl)-7-triethylsilyl-baccatin III | 185850-96-8

• 英文名称: 2-debenzoyl-2-(3-methylbutanoyl)-7-triethylsilyl-baccatin III
• CAS: 185850-96-8
• 化学式: C₃₅H₅₆O₁₁Si
• 分子量: 680.909
• InChiKey: YKGZNILNHNTUHC-WNZPWSLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  47.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  154.89
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-debenzoyl-2-(3-methylbutanoyl)-7-triethylsilyl-baccatin III 在 吡啶 、 氢氟酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 3.33h， 生成 10-acetyl-2-debenzoyl-3'-dephenyl-3'-(2-methylprop-1-enyl)-2-(3-methylbutanoyl)docetaxel
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Nonaromatic Taxoids:  Effects of Alkyl and Alkenyl Ester Groups on Cytotoxicity

  摘要：

  Several new nonaromatic taxoids are synthesized by means of the beta-lactam synthon method. These include taxoids modified with 3-methylbut-2-enoate, 3-methylbutanoate, and cyclohexanecarboxylate groups in place of the benzoate at the C-2 position. In addition, taxoids with 2-methylprop-1-enyl, 2-methylpropyl, (E)-prop-1-enyl, and cyclohexyl groups at the C-3' position are also prepared in combination with the modifications at C-2. The alkyl and alkenyl ester groups at C-2 displayed pronounced effects on the in vitro cytotoxicity. Two of the fully aliphatic taxoids possess similar or stronger activity than paclitaxel and docetaxel. It is clear that the 2-benzoate does not play a unique role, and replacement with the appropriate alkyl and alkenyl groups provides taxoids with equivalent or superior activity.

  DOI：

  10.1021/jm9606711
• 作为产物：
  描述：

  3,3-二甲基丙烯酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 2-debenzoyl-2-(3-methylbutanoyl)-7-triethylsilyl-baccatin III
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Nonaromatic Taxoids:  Effects of Alkyl and Alkenyl Ester Groups on Cytotoxicity

  摘要：

  Several new nonaromatic taxoids are synthesized by means of the beta-lactam synthon method. These include taxoids modified with 3-methylbut-2-enoate, 3-methylbutanoate, and cyclohexanecarboxylate groups in place of the benzoate at the C-2 position. In addition, taxoids with 2-methylprop-1-enyl, 2-methylpropyl, (E)-prop-1-enyl, and cyclohexyl groups at the C-3' position are also prepared in combination with the modifications at C-2. The alkyl and alkenyl ester groups at C-2 displayed pronounced effects on the in vitro cytotoxicity. Two of the fully aliphatic taxoids possess similar or stronger activity than paclitaxel and docetaxel. It is clear that the 2-benzoate does not play a unique role, and replacement with the appropriate alkyl and alkenyl groups provides taxoids with equivalent or superior activity.

  DOI：

  10.1021/jm9606711